HCID 12150687, compound → HCID 10112900, compound

HRID 2086169Notes

Reaction equation

HRID 2086169 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([CH3:15])[C:11]([O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH:24]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[OH:25])[CH:18]=1)=[C:10]([CH3:33])[CH:9]=2)=[O:5])C>CO.O.[OH-].[K+]>[F:32][C:29]1[CH:30]=[CH:31][C:26]([CH:24]([OH:25])[C:19]2[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=2[OH:23])[O:16][C:11]2[C:12]([CH3:15])=[C:13]3[C:8](=[CH:9][C:10]=2[CH3:33])[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]3)=[CH:27][CH:28]=1

Participants

5

Reactant 1

HCID 12150687HCID 12150687, compound

Product 1

HCID 10112900HCID 10112900, compoundYield 79.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent2×

Procedure

To a solution of 5-{3-[(4-Fluoro-phenyl)-hydroxy-methyl]-4-hydroxy-phenoxy}-4,6-dimethyl-1H-indole-2-carboxylic acid ethyl ester (17.5 mg, 0.039 mmol) in a mixture of methanol (0.5 mL) and water (0.5 mL) at room temperature was added potassium hydroxide (3M, 0.078 mL), and the resulting solution was stirred at room temperature for 20 hours. The reaction solution was diluted with 0.1M potassium hydroxide (10 mL) and washed with ethyl acetate (3 times 5 mL). The aqueous solution was acidified with hydrochloric acid and then extracted with ethyl acetate (3 times 10 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to afford the title compound (13 mg) as a solid. 1H NMR (400 MHz, CD3OD) δ11.0 (s, 1H), 7.30-7.26 (m, 2H), 7.12 (s, 2H), 6.93 (t, 2H), 6.73 (d, 1H), 6.60 (d, 2H), 6.43-6.40 (dd, H), 5.97 (s, 1H), 2.23 (s, 3H), 2.13 (s, 3H). MS (APCI−) Calc:421. 1, Found: 420.1 (M−1).

Workup

  1. washwashed with ethyl acetate (3 times 5 mL)
  2. extractionextracted with ethyl acetate (3 times 10 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3f3de808fdcf4914b87b8051aff9c1e3
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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